Playboy Interview: Stephen Colbert

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Photography by David Rose

One of the most controversial political attack ads of the year didn’t originate with an actual candidate or political party. It came from Stephen Colbert. Or more accurately, “Stephen Colbert,” his satirical alter ego. The ad was funded by Americans for a Better Tomorrow, Tomorrow, a super PAC formed by Colbert as part of his “exploratory committee to lay the groundwork for [his] possible candidacy for president of the United States of South Carolina.” The super PAC ad suggested, in no uncertain terms, that presidential hopeful Mitt Romney might be a serial killer. “He’s Mitt the Ripper,” the voice-over declared. When asked about the ads by George Stephanopoulos on ABC’s This Week, Colbert (or “Colbert”) claimed ignorance. “I had nothing to do with that ad,” he said. Technically he was following to the letter the rules of super PACs, which are allowed, thanks to a Supreme Court ruling, to raise unlimited funds for attack ads without being directly connected to a campaign or candidate.

“I don’t know if Mitt Romney is a serial killer,” he told Stephanopoulos. “That’s a question he’s going to have to answer.… I do not want any untrue ads on the air that could in any way be traced back to me.”

It was brilliant political satire—earning Colbert a prestigious Peabody Award, his second—that crossed into the realm of performance art. Colbert mocked the system from within, using himself as a comedic straw man. Although Colbert’s main gig is behind a desk as host of Comedy Central’s faux pundit news show The Colbert Report, it wasn’t the first time he’d blurred the line between satirist and subject. Colbert has mocked President George W. Bush to his face at the White House Correspondents’ Dinner, testified before the House Subcommittee on Immigration (where he called for Americans “to stop eating fruits and vegetables”) and co-hosted with The Daily Show’s Jon Stewart a political rally on the National Mall that attracted an estimated 215,000 participants.

Born in Washington, D.C. and raised in Charleston, South Carolina, Colbert was the youngest of 11 kids. He had a happy childhood, at least for the first decade of his life. But in 1974, when he was 10 years old, his father, Dr. James Colbert, and his two brothers closest to him in age—Peter, 15, and Paul, 18—were killed in an airliner crash. Colbert found solace in science fiction and acting. He ended up in Chicago, studying theater at Northwestern University and joining the Second City comedy theater. He was hired as a correspondent and writer by The Daily Show in 1997, where he stayed for nine years before the network offered him The Colbert Report. Within a year, Colbert was averaging 1.5 million viewers a night. In April he was named one of Time magazine’s 100 Most Influential People in the World.

The 48-year-old comedian has two best-selling books, I Am America (and So Can You!) and the children’s book I Am a Pole (and So Can You!), and a new book, America Again: Re-Becoming the Greatness We Never Weren’t. He enjoys a quiet home life in Montclair, New Jersey with his wife, Evelyn—an actress he met in 1990—and their three children, Madeline, Peter and John.

We sent writerEric Spitznagel, who last interviewed Charlie Sheen for Playboy, to talk with Colbert. He reports: “I met Colbert at his studio office in New York’s Hell’s Kitchen. I’d actually met him before, back in 1992, when I was a newly minted box-office employee at Second City in Chicago and he was in his final months performing with the main-stage cast. As we talked, Colbert sat behind his desk, his most recent Peabody in front of him, and outside the open window behind him an American flag fluttered in the breeze, perfectly positioned over his right shoulder in a way even his fictional doppelgänger couldn’t hope to choreograph.”

PLAYBOY: When people meet you for the first time, which version do they want, Stephen Colbert or “Stephen Colbert”?

COLBERT: I think they always want to meet the guy who’s going to show up and tell jokes. But if I’m asked to do something that isn’t specifically a performance, then I have to be very specific that he’s never going to show up.

PLAYBOY: “He” being the other Stephen?

COLBERT: That’s right. If I’m doing a talk show or an interview like this, or pretty much anything where I can’t control the context, I’m loath to do the character.

PLAYBOY: Why?

COLBERT: Because outside the context of the show, you have to be okay with the clang of him against reality.

PLAYBOY: But isn’t that what makes him funny?

COLBERT: Yeah, but that doesn’t always work in a different context. We create our own reality on the show. I’m in a cocoon of the character’s creation. Even within that reality, he’s in a cocoon. Unless I’m doing something like the Correspondents’ Dinner, testifying before Congress, doing the rally or something where I’m purposively injecting myself into a story, there’s no benefit to pushing him up against reality. While I’m an improviser and enjoy discovery, the show follows a script. I have a pretty good idea what’s going to happen. It’s a very crafted, controlled environment.

PLAYBOY: You can’t control what happens with the guests, can you? They’re not following a script.

COLBERT: No, but they’ve all been warned. I tell everybody the same thing: “I do the show in character, and he’s an idiot.”

PLAYBOY: Is that still necessary? Do people come on The Colbert Report and not know what to expect?

COLBERT: It’s usually someone from another country or from a rigorous academic discipline who doesn’t have a lot of time for TV. Mostly I tell them because it’s a ritual for me. I have to remind myself what I’m about to do, because I rarely hit it as hard as I used to.

PLAYBOY: Why not?

COLBERT: It’s hard to remember. Often I’m just very interested in what my guests have to say. You have to be vigilant to stay ignorant.

PLAYBOY: Your guests have to be willing to play along too.

COLBERT: They do, yes. That’s what I tell them before the show. I tell them, “He’s willfully ignorant of what you know and care about. Honestly disabuse him of his ignorance and we’ll have a good time.” The important thing in that sentence is [speaks slowly] “honestly disabuse him of his ignorance.” Actually tell him why he’s wrong. Hopefully that makes it easier for the guest. All they have to do, as my guest producer Emily Lazar says, is talk to him as though he’s a harmless drunk at the next bar stool.

PLAYBOY: That can still be intimidating. You’re essentially asking them to walk into an argument.

COLBERT: Yeah, but it’s an argument with an idiot. Some people perceive me as an assassin or at least someone who can slip under your guard with a knife. But if you watch what I do, that’s almost never the case. I’m just trying to keep the balloon in the air. It rarely turns into anything combative. It’s mostly just silly, or it’s my character expressing his ignorance on a difficult or not-at-all difficult subject. It’s an opportunity to knock down common ignorances. And I would pray that guests do that.

COLBERT: I wouldn’t put that on my business card, nor would I make it my campaign slogan if I were Jim Moran. I suppose the consensual part was him being unbelievably playful. He was up for anything, even after I called him a poor man’s Ted Kennedy.

PLAYBOY: If people think you’re an assassin or that being on the show is like rape, why do they do it? What’s the benefit for them?

COLBERT: I don’t know. Maybe they have a book to sell. I hope that perception is starting to change. I think politicians are the only ones who are wary about us. That’s why we get almost no conservatives anymore. Even conservative pundits are hard to come by, which is too bad.

PLAYBOY: Who’s your ideal guest?

COLBERT: We want someone who represents something, who feels strongly about what they’re talking about and will allow for a little dramatic friction. The most disappointing guest is somebody who won’t be their personality.

PLAYBOY: What does that mean? How can you not be your personality?

COLBERT: Take Mr. Bill O’Reilly. He was a perfectly lovely guest, but he wouldn’t be his personality. He wouldn’t be the guy he is on his show. And I don’t know why. I went on his show, and I was my personality. That was our deal; I’d go on his show and he’d come on mine. But he came on my show and he wasn’t his personality. He wasn’t an unpleasant person. He’s a perfectly fine guest and I have no complaints other than the fact that I booked Bill O’Reilly and I got William O’Reilly.

PLAYBOY: Did he give you any advice? Any words of wisdom from one pundit to another?

COLBERT: He said, “Watch your guest list. If you book the same kind of people over and over—Al Franken, Keith Olbermann—people notice that pattern.” I told him, “Oh, Bill, I toy with those guys. I’m slapping them around.” He said, “I know, but not everybody is watching your show as closely as I am.” I was like [clasps hands and holds them to his chest], “I’ve totally made it!” That was about five, six months into the show.

PLAYBOY: One of your friends from high school said you once joked about starting a cult. Is that true?

COLBERT: Yeah, that was an L. Ron Hubbard reference. I was with a bunch of guys—we were all science fiction fans—and we were sitting around one day, drinking beer or doing something we weren’t supposed to be doing, talking about power. The question posed was, If you wanted power over people, what would you do? What career would you pursue? I remember one guy, who’s actually a colonel now, said, “If I wanted real power, I wouldn’t be a politician. I’d be in the Joint Chiefs of Staff.” It got around to me, and I said, “Well, I think I would probably major in psychology and start a cult.” [laughs] There’s something enjoyable about cults to me.

PLAYBOY: Enjoyable?

COLBERT: I’m interested in what makes someone a cult figure and what engenders cult adherence, what engenders that behavior.

PLAYBOY: Are you surprised people are drawn to cults?

COLBERT: Not surprised. I’m fascinated. I’m fascinated that people want to know what to do. And people want to know what to think. And people want to know how to feel. Not just what to feel but how to feel.

PLAYBOY: Do you think that’s unnatural?

COLBERT: No, it’s completely natural. I’m surprised there aren’t more unbalanced people in the world, because being alive is not easy. We’re just not that nice to one another. We’re all we have, and Jesus, are we shitty to one another. We really are. The only thing that keeps us going back to one another is that we’re all filled with such enormous self-doubt. We have doubts about our ability to be alone, to self-actualize. We’re on such a rocky road all the time. Every moment is new. Every inch of the mountain is fresh snow. If someone said, “I have been out ahead and I know what you’re supposed to do,” if I believed that were true, I would absolutely obey whatever father told me. I would stay on the compound.

PLAYBOY: You would just as happily be a cult member as a cult leader?

COLBERT: I’d love to be a cult member, just another loyal follower. It sounds very comforting.

PLAYBOY: The Colbert Nation could arguably be described as a cult.

COLBERT: In the loosest possible sense. It’s an ironic cult.

PLAYBOY: But your audience listens to you. It may be a joke, but it’s a joke with a lot of followers.

COLBERT: Which is not what we set out to do. When we started the show, we wanted it to have a mythos that would never be real. We’d play on the difference between reality and my character’s perception of reality.

PLAYBOY: He would think he had influence but he really didn’t?

COLBERT: Exactly. He thinks he says things and people listen and take action. He has a nation, this army he can mobilize. We were already too successful for that joke, to play on the vast difference in status between thinking you’re a prophet and being on a show that nobody watches.

PLAYBOY: Because people were actually watching, and they got the joke.

COLBERT: Not only did they get it, they were willing to play along. I’m constantly awed by their willingness to play along with almost anything. They actually cheer things they don’t believe in because my character says it. You know what I mean? I have a generally liberal audience, but they will applaud when I nail a liberal lion because they want my character to win. It’s a strange relationship that seems natural now, but every so often I have to remind myself that this is not normal. This is not common.

PLAYBOY: Will they do pretty much anything you say, or are there rules and parameters?

COLBERT: I put a lot of thought into the ways we engage with them. [laughs] I always say “we,” like “We’re pregnant.” But there are a lot of people involved. It’s not just me, by any means. With the audience, we think about things like whether we are dictating their actions or inviting them to take action. Dictation of action is not nearly as fun for an audience. We’ve done it sometimes, and it’s been a mistake. It’s much better to invite them to be part of an action rather than saying, “I command you to do this.” The other thing is, you have to follow through. If you initiate a game and they take part, you can’t stop until it reaches a mutually satisfying resolution.

PLAYBOY: The Colbert character is obsessed with fear. He even had a rally in Washington, “Keep Fear Alive.” Why is fear so intoxicating?

COLBERT: I suppose fear is like a drug. A little bit isn’t that bad, but you can get addicted to the consumption and distribution of it. What’s evil is the purposeful distribution of fear. As Paul said when he was faced with the gom jabbar, “Fear is the mind-killer. Fear is the little death that brings total obliteration.”

PLAYBOY: Did you just make a Dune reference?

COLBERT: I did! [laughs] If you’re injecting fear into other people, then you’re trying to kill their minds. You’re trying to get them to stop thinking. That’s antithetical to the founding of this country. It’s on the Jefferson Memorial. I’m stealing this from Jefferson, but I’m also stealing it from the movie Born Yesterday. Bill Holden takes Judy Holliday to the Jefferson Memorial, and they read the inscription together. “I have sworn upon the altar of God eternal hostility against every form of tyranny over the mind of man.” Fear is an attempt to impose tyranny over someone’s mind. It’s an act of oppression.

PLAYBOY: We know what Stephen Colbert the character is afraid of, or trying to make us afraid of.

COLBERT: Everything.

PLAYBOY: Bears, jazz robots, happiness.

COLBERT: [Laughs] The list is endless.

PLAYBOY: But what about you? What are you, the real Stephen Colbert, afraid of?

COLBERT: I really like boats. I was driving a boat this summer with my family and some friends. About a quarter mile away there was a channel marker, and I was heading straight for it. Now there is no way on God’s green earth that I would not have seen that channel marker in the 45 seconds it would have taken me to get to it. But at the second it appeared I wasn’t looking up. I was looking at my instrument panel. Then I looked up and my wife said, “You see the channel marker, right?” And I said, “Of course.” But I actually hadn’t seen it yet. I have no doubt that everything would have been fine, but in my mind I see myself for the next 45 seconds, I don’t know, somehow…closing my eyes and slamming into the channel marker with a boat full of friends. [pauses] I don’t know what that means.

PLAYBOY: That’s an incredibly specific fear.

COLBERT: It really is. [laughs]

PLAYBOY: You could have just said “drowning.”

COLBERT: I don’t like spiders. How about that?

PLAYBOY: That works.

COLBERT: I actually don’t like bears.

PLAYBOY: Seriously? Like your character?

COLBERT: I don’t dislike bears, but I am kind of afraid of them. There was a time when, if I had dreams about bears, something bad was going on in my life.

PLAYBOY: How did bears become a recurring motif on the show? Was it just to have something to talk about that wasn’t topical?

COLBERT: For the very first show, we were trying to find something that had a repeatable structure. We had this bit called “ThreatDown,” when he talks about the number one threat to America that week. We were considering another story, something from Florida about a Burmese python that had grown to 13 feet long and swallowed an alligator and the alligator had eaten its way out of the snake. It was a really crazy story with horrible pictures. Then a bear story came up that wasn’t as flashy, but we went with it. Partly because bears are very resonant to me, because I really do have a bit of a bear problem. And it just seemed like a richer fear to us. We always said that anything my character is concerned about qualifies as news. If he says bears are the number one threat to America, then that is the case.

PLAYBOY: He’s justifying his own anxieties?

COLBERT: Exactly. “I want to make you afraid of the things I’m afraid of.”

PLAYBOY: Do you feel tied to the news cycle? When you’re doing political comedy, a joke may be funny in the morning and irrelevant by that afternoon.

COLBERT: There’s a good and a bad in that. We are the shadow cast by real people. And that shadow changes shape as the news cycle changes shape, so you always have fresh dirt to dig in. That’s exciting. Like with this presidential race. It’s as simple a narrative as any made-for-TV movie: two men, one victorious.

PLAYBOY: So how do you deal with that?

COLBERT: We know everything that happens structurally between here and there. You just prepare yourself to collect the news on the dates that are preordained. There are surprises, but there’s a tent pole of a narrative between today and the inauguration. But we also try to release ourselves from that. We don’t need to follow what everyone says is the story. Not because we’re mavericks but because sometimes the story holds no interest for me. I’m perfectly happy to talk about a story that’s not necessarily timely or newsworthy but is just interesting to me. Like super PACs.

PLAYBOY: Super PACs aren’t newsworthy?

COLBERT: They’re newsworthy, but they weren’t in the news. Not many people at the time were talking about super PACs, at least not in the mainstream media. Most people had no idea what they were, so for the first six months we had to explain them to the audience every time I brought them up. That process of educating the audience is really educating ourselves.

PLAYBOY: But you took it one step further and started your own super PAC.

COLBERT: We did, yeah.

PLAYBOY: Isn’t that unnecessarily complicated? Why not just make jokes about super PACs in the abstract? Wouldn’t that be easier, and cheaper?

COLBERT: It would be, absolutely. But I have an opportunity as this character to do things. I have an opportunity to do things that lead to discovery.

PLAYBOY: For you or the audience?

COLBERT: For me and the audience. If you just talk about it, everyone sits on their hands and the reality of it just watches as you talk about it. But by putting yourself in it, reality has to respond to your actions. I don’t pretend that the camera doesn’t change things. But it’s a version of reality that allows us to show what normally doesn’t get seen.

PLAYBOY: How much money did you ultimately raise for your super PAC?

COLBERT: About $1.4 million. We’ve got somewhere between $850,000 and $900,000 left. We’ve spent about half a million dollars of it so far. Because running for president—or not running for president, whatever it was we did—is expensive. But I can spend it on anything I want. I could use my super PAC money to buy a private jet, and I have to justify it to no one. I wouldn’t have known that unless I had my own super PAC. That’s the great thing about throwing yourself into the story. You find out things you wouldn’t have known otherwise.

PLAYBOY: Have you always had this curiosity? As a kid, did you get the same excitement from digging into a complicated subject and trying to figure out how it ticks?

COLBERT: To some extent, sure. Any curiosity I have probably comes from my dad. He was a big thinker, a true intellectual. His idea of a good time was to read French philosophy, often French Christian philosophy.

PLAYBOY: Did he have strong political opinions?

COLBERT: I don’t really know. The only bumper sticker my parents ever had just said “Kennedy.” That’s all it said. And my father was I think president of Physicians for Kennedy. We have a picture of my father and President Kennedy at the White House. My father had just come out of a rainstorm. He’s soaking wet and wearing a raincoat. Kennedy is shaking his hand and my father is just laughing. That’s the only political involvement I know about. Otherwise, I think my parents were pretty conservative.

PLAYBOY: Were your parents funny?

COLBERT: My mom is very warm and funny and quick to laugh and quick to hug and kiss. My father died when I was pretty young, so I don’t remember any specific jokes, but he certainly encouraged us to be funny. But my brothers and sisters are the funniest people in the world to me. I have comedy influences, other comics I really like, but none of them is as influential as those 10 people above me. I’ve had people say, “Oh, you’re the baby. You have a built-in audience.” But I was their audience.

PLAYBOY: What kind of comedy did the Colbert kids enjoy? Slapstick, wordplay?

COLBERT: Everything. Every one of them is different. Some are great at telling stories. Some are into jokes. For my brother Billy it was all about jokes. “A guy walks into a bar.” And W.C. Fields. He had W.C. Fields posters all over his room. If there was a W.C. Fields festival on television, he would force me to watch it. “You have to watch this pool cue trick that he does.” Or Gahan Wilson. Billy was a huge Gahan Wilson fan. It was very dark comedy, and I was a little kid, but he’d show me all these Gahan Wilson cartoons. And he taught me how to juggle. [laughs] My brother Billy was a big comedic influence.

PLAYBOY: When did you think you might want to be more than just an audience member?

COLBERT: It was when we were driving back from my father’s funeral. He was buried in Annapolis, and we were all driving home in a funeral limo. I don’t know if that’s what they’re called. It’s a limo with the jump seats that face front and back, like the presidential limo where the aide is talking to the president. You know what I’m talking about? In those espionage movies, right before the aide shoots the president and you find out he’s really a Russian spy or whatever. It’s that Mission Impossible style of limo.

PLAYBOY: We know what you mean.

COLBERT: One of my sisters, I think it was Mary, made a joke to Margo. Or it could have been Lulu to both of them. I don’t remember. One of them made Margo laugh so hard, she snorted and fell on the floor. There was enough room between the seats to actually fall on the floor of this limo.

PLAYBOY: Do you remember the joke?

COLBERT: [Pauses] I don’t, but I remember the laughter. I remember thinking [softly] I would like that. That connection.

PLAYBOY: Your father and two brothers died when you were just 10.

COLBERT: That’s right.

PLAYBOY: They were on a commercial airliner that crashed while landing in thick fog. Your brothers were both teenagers, and your father was taking them to Connecticut to enroll them in private school. How did you make sense of their deaths?

COLBERT: Things didn’t seem that important anymore. Nothing seemed that important anymore. My mother said to me—and I think she said this to all my brothers and sisters—she urged me to look at everything in the light of eternity. In other words, it doesn’t matter what I wear. I just wear the uniform of my youth. I wear an oxford-cloth shirt and khakis. What does it matter? What does it matter what I wear?

PLAYBOY: As a 10-year-old boy who just lost his dad, that advice helped you?

COLBERT: Sure, absolutely.

PLAYBOY: It’s been almost four decades since it happened. Does the grief dissipate?

COLBERT: No. It’s not as keen. Well, it’s not as present, how about that? It’s just as keen but not as present. But it will always accept the invitation. Grief will always accept the invitation to appear. It’s got plenty of time for you.

PLAYBOY: “I’ll be here.”

COLBERT: That’s right. “I’ll be here when you need me.” The interesting thing about grief, I think, is that it is its own size. It is not the size of you. It is its own size. And grief comes to you. You know what I mean? I’ve always liked that phrase He was visited by grief, because that’s really what it is. Grief is its own thing. It’s not like it’s in me and I’m going to deal with it. It’s a thing, and you have to be okay with its presence. If you try to ignore it, it will be like a wolf at your door.

PLAYBOY: It’s a loud wolf. It huffs and it puffs.

COLBERT: [Laughs] It does, doesn’t it? It can rattle the hinges.

PLAYBOY: Not long after their deaths, you immersed yourself in science fiction.

COLBERT: It was right after we buried my father and brothers. I was staying with my brother Ed, who’s 18 years older than I am and was married with kids. I was in their guest bedroom, where they kept stacks of science fiction books. I just randomly picked up The Long Arm of Gil Hamilton by Larry Niven. I read it and loved it. From there I just dove into the world of science fiction. When I was 13, one of my friends pressed into my hands The Lord of the Rings and said, “You’ve got to read this.” And I loved it. As you can tell, I’m a little obsessed. [points to a Lord of the Rings pinball machine in the corner of his office]

PLAYBOY: What appealed to you about the books as a teenager?

COLBERT: In some ways it was about escape. I think there’s absolute truth in escaping the reality of your present predicament. And that can just be about being young. It doesn’t have to be tragedy. There’s a tragedy to being 13. Things are changing. Friends are changing. Your body is changing. You need to escape that. My additional emotional crises don’t necessarily explain my interest in it.

PLAYBOY: Didn’t you visit the Hobbit film shoot in New Zealand?

COLBERT: I did. [Director] Peter Jackson invited me to the set last year. I flew out and watched them shoot some scenes and went to some locations. I saw a 25-minute cut, and it was amazing. Jackson knows I’m a big fan of the films.

PLAYBOY: You flew out to New Zealand just to watch? He didn’t hire you as an extra or something?

COLBERT: [Smiles]

PLAYBOY: Are you telling us you’re in the Hobbit movie?

COLBERT: Could be. [smiles]

PLAYBOY: Can you elaborate?

COLBERT: [Fumbles with paper on his desk] So, uh, I was just writing Mr. Jackson a note to congratulate him on making The Hobbit into three movies. Because I think that’s just fantastic.

PLAYBOY: You’re not going to tell us anything, are you?

COLBERT: [Smiles, says nothing]

PLAYBOY: You sneaky bastard.

COLBERT: You were asking how the book affected me as a teenager.

PLAYBOY: Sure, let’s talk about that.

COLBERT: I think [Lord of the Rings character] Aragorn is the model of manhood. He’s the Apollonian ideal. He’s a warrior, a scholar, a poet, a healer. He’s all things you can aspire to be. As a kid I thought I wanted to be like that.

PLAYBOY: But it wasn’t all science fiction and fantasy for you. You also had a collection of Bill Cosby stand-up records.

COLBERT: Yeah, after the boys died, I inherited their record collection. I had Bill Cosby Is a Very Funny Fellow…Right! and Wonderfulness, and I listened to them over and over and over again, every night. [pauses, looks at his feet] I just wore them out.

PLAYBOY: Do you still have them?

COLBERT: Not the originals, no. But somebody sent me those two albums on CD, as a thank-you for something. I have them on my iPod now, and I can do every joke. I can do every joke with the exact same rhythm and timing that Mr. Cosby does them, after 30 years of not listening to them, because they were so deeply ingrained in me. The funny thing is, the albums were so scratched that I missed entire punch lines. He’d be doing a setup, and then it would skip ahead to a huge laugh. And in my mind I was like, what could that punch line have been? I was writing Bill Cosby’s punch lines in my head.

PLAYBOY: Now that you’ve heard the CD versions, were you close?

COLBERT: Not at all. [laughs] My jokes were so far off.

PLAYBOY: Were those albums the only things you inherited from your brothers?

COLBERT: No, I got clothes and all kinds of things. I still have…I still have my brother Peter’s belt. I’ve been carrying it in my closet since I was 10. I didn’t even realize I’d been holding on to it until last year, when my son Peter had to go off to school one day.

PLAYBOY: Your son is also named Peter?

COLBERT: Yeah. I think it was a school concert, and he had to wear a belt and couldn’t find his. I said, “Oh, I have something that might fit you.” I went and found it and put it on him. It was a small belt. Peter was a skinny guy. I belted it on my son and my wife, Evie, said, “Where did this belt come from?”

PLAYBOY: Was that when you realized?

COLBERT: Yeah. I said, “Oh, that’s Peter’s.” And she said, “You have your brother’s belt?” And it occurred to me at that moment that I had moved that belt from closet to closet for 37 years without telling anyone, not even my wife, whom I’ve known for 20 years. We moved many times, and in every new house I’ve been [mimes clicking the belt onto a hook].

PLAYBOY: That makes sense. What were you going to do, throw it away?

COLBERT: That’s exactly it! What do you do with these things? The other day I thought, I wonder what happened to that belt. And I realized that I don’t care. Now I don’t care.

PLAYBOY: Because you gave it to your son?

COLBERT: Because it got used. It got used. I remember when I was a teenager, I went skiing in Vermont. I had an aunt up there, my mother’s older sister, who lived in Plainfield and was a dairy farmer. You need goggles when you ski, and I wore my uncle Eddie’s goggles. These were black, heavy rubber goggles, with dark green lenses. He wore them while he was a paratrooper in the 101st Airborne.

PLAYBOY: The Screaming Eagles?

COLBERT: That’s right. He died in the war. These were the goggles he wore on D-Day, and I would ski in his goggles. I remember on one of these ski trips, I lost the goggles. I had to tell my mom. I was devastated. And she said to me, “These things are to be used.”

PLAYBOY: She sounds like a wise woman.

COLBERT: She is.

PLAYBOY: Was she supportive of your becoming an actor?

COLBERT: Absolutely. She had wanted to be an actress at one point in her life. She spent a lot of her college years doing theater, but then she got sick. She was bedridden for much of a year. When she recovered, my father said, “Let’s get married.” And they did, and she never did theater again. Her mother wanted to be an actress too, but that was very frowned upon in my grandmother’s day. Being an actress was akin to being a streetwalker.

PLAYBOY: So you have acting in your DNA?

COLBERT: I do. My mother always loved acting and taught us as kids how to do falls.

PLAYBOY: Pratfalls?

COLBERT: Right. She would be in the kitchen and she’d suddenly just faint in a swoon, put a hand on her forehead and fall backward like this [demonstrates a melodramatic swoon], like Cleopatra learning of the loss of Antony or something. She would teach us to do the roll-down so you wouldn’t hurt yourself as you fell. “Remember, it’s ankle, knee, hip, chest, arm, head.” We all learned how to do the falls. And we’d fall all over the house, all the time, and my mom was fine with it. I guess that love for all things theatrical just rubbed off on me. Also, I met my wife at the theater because of my mom.

PLAYBOY: How so?

COLBERT: She had an extra ticket to the Spoleto Festival in Charleston. She asked if I wanted to go, and I said sure. I walked into the theater, and there across the lobby was my wife. I thought, Oh, wow, there’s my wife.

PLAYBOY: You knew immediately?

COLBERT: There was never a doubt in my mind.

PLAYBOY: Did you talk to her first, or did she talk to you?

COLBERT: [Laughs] That’s a two-hour story, I’m afraid. It really is. People who have heard the whole story—and it’s not a bad story; it’s a good story—will later say to Evie, “Stephen told me the story of how you guys met.” And Evie will go, “I’m so sorry.” I can’t start it and leave out any details, because to me it’s somewhat miraculous that we’re married. Let’s just say I met her at a theater and leave it at that.

PLAYBOY: Didn’t she know Jon Stewart before you did?

COLBERT: She did. She was an actress living in New York, on the Lower East Side in Alphabet City. Jon was a young guy trying to do comedy in New York. A friend of Evie’s, her roommate, dated Jon’s roommate. Or something like that. So Jon ran in her social circle. It was this gang of people who hung out, some of whom came to New York to be actors, some of whom came to do architecture. They were all University of Virginia people. Some just came to New York to be part of the go-go 1980s. It was very Bright Lights, Big City.

PLAYBOY: Was there lots of cocaine and recreational sex?

COLBERT: [Laughs] I don’t know what they were doing. Jon just remembers the world not being enough for these people. Evie remembers Jon being a quiet guy. He was the one nursing a beer in the corner. And not funny. He was not the funny one. A nice enough guy, but his friend was the funny one. When Jon got the gig on The Daily Show years ago, Evie was like, “Jon Stewart? He’s not funny.” [laughs] She likes to lord that over me. “Oh, I knew him long before Stephen did.”

PLAYBOY: Is it true you met Stewart for the first time while asking him a question at a press conference?

COLBERT: Yeah, that was it. I’d been doing The Daily Show when Craig Kilborn was hosting. I heard they were doing a press conference to announce that Jon was the new host, and I said, “Isn’t that the sort of thing we should be covering?” So I went, sat down in the audience and raised my hand when they opened it up to questions. I was like, “Stephen Colbert, Daily Show.” Oh God, how did I phrase it? “Does this announcement have any effect on the prospects of me getting the hosting job?” Jon looked at Doug Herzog, who was the network president at the time and is again, and said, “You said he wasn’t funny.”

PLAYBOY: Are you and Stewart friends or just friendly?

COLBERT: We’re actually friends.

PLAYBOY: When it’s just the two of you, do you talk about politics?

COLBERT: Not politics specifically, but we’ll talk about the news. We also talk about our families. We talk about anything friends talk about. That’s grown over the years. I’m an ardent admirer of his. I would say the thing that has kept me from being as good a friend to Jon as I would like is just that I am such a fan. I am gobsmacked by his abilities. But that being said, we go out to dinner, and we sometimes pick up the phone just to say, “How are you?” Or, “Do you mind if I tell you how I am? I had a shitty week.”

PLAYBOY: It can be shitty sometimes?

COLBERT: Rarely, but yeah, it happens. That’s another reason not to be tied to the news cycle. It’s damned depressing. I have no interest in behaving or thinking cynically. But it’s an easy trap to be cynical about anything, certainly when you’re talking about politics or the media.

PLAYBOY: Doesn’t comedy require a little cynicism?

COLBERT: Not really. I believe that people, more often than not, act with the best possible intentions. And when they don’t, that’s funny to me. That’s why comedy ends up seeming cynical, because you’re talking about the gap between what people say and what they do. You seem cynical because you’re always talking about that selfish behavior that’s dressed up as altruism. It doesn’t mean there isn’t altruism. It just means that it’s harder to make jokes about altruism.

PLAYBOY: There have been quite a few books written about you.

COLBERT: I heard that that exists.

PLAYBOY: There’s America According to Colbert, The Stewart/Colbert Effect, Colbert’s America: Satire and Democracy. The list goes on and on.

COLBERT: It’s all poison to me.

PLAYBOY: Poison? How is it poison?

COLBERT: Other people’s deconstruction of your motivations doesn’t help you do what you do. You can’t swallow and think about swallowing at the same time.

PLAYBOY: You don’t think about why a joke works or doesn’t work?

COLBERT: I do sometimes. Comedians dissect jokes all the time. Comedians are beautiful structuralists. But ultimately it’s an athletic endeavor. You have to be able to just hit the backhand. You can’t think about all the pieces of it. You can’t think about your swing. You just have to do it. Reading someone else’s deconstruction of what I do, all it does is put me in my head. On nights when the show goes particularly well, I am not aware of its fluidity. A lot of nights I’m just worried that I’m not going to be as good as the script in front of me.

PLAYBOY: You have more faith in the script than your own abilities?

COLBERT: There’s a great book called The Lyre of Orpheus by Robertson Davies, a Canadian writer. In it someone has written a symphony. It’s part of her doctoral thesis, and she brings it to a professor, who says, “Okay, I’ll let you know what I think.” He’s asked, “Don’t you want to hear it?”—there’s an orchestra at this school—and the professor says, “No. All an orchestra can do is get the notes wrong. I’ll play it perfectly in my head.” I understand what that means. When I look at a script for one of our shows, I’m playing it perfectly in my head. All I can do is fuck it up.

PLAYBOY: You recently extended your contract with Comedy Central through the end of 2014. Is it exhausting to think about doing The Colbert Report for another two years?

COLBERT: I try not to think about it in terms of years. You can’t do 161 shows. It can’t be done. All I can do is today and tomorrow and have some idea of what we’re doing next week. That’s all I can worry about. I have a script for today, I have probably half a script for tomorrow, and that’s as far down the road as I ever look. I know the mechanism of my show, and I know how it works. There’s a joy in that.

PLAYBOY: You’ve called the process of making The Colbert Report “the joy machine.”

COLBERT: It still feels that way. I have no fear of doing the show. I have no exhaustion in doing the show. I have no idea what’s going to happen tomorrow. I can’t predict what we’ll be trying to make jokes about in the next six months. I don’t know what the next super PAC game will be for us or who will win the election. You can’t plan for any of that. If I thought I knew what was going to happen, it wouldn’t be worth doing. The challenge is how joyfully, with what sense of fun and adventure and playfulness, we will greet it. We don’t have to look for what the next thing will be. If experience is any judge, it’ll come flowing toward us like a river.